Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH08515
RESEARCH ARTICLE
Contents Vol 62(2)

Fluoroquinolones from Imidoylketenes and Iminopropadienones, R–N=C=C=C=O

Belinda E. Fulloon A and Curt Wentrup A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

B Corresponding author. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 62(2) 115-120 https://doi.org/10.1071/CH08515
Submitted: 24 November 2008  Accepted: 18 December 2008   Published: 19 February 2009

Abstract

3-Fluoro-, 4-fluoro-, and 2,3,4-trifluorophenyliminopropadienones have been generated by flash vacuum thermolysis (FVT) of 5-[(fluoroarylamino)methoxymethylene]-2,2-dimethyldioxan-4,6-dione (Meldrum’s acid) derivatives. Their reaction with methanol affords interconverting imidoylketenes and oxoketenimines, which are employed in a synthesis of fluoroquinolones. The same quinolones are obtained from methyl 1-fluoroaryl-1,2,3-triazole-4-carboxylates, which on FVT eliminate N2 to generate oxoketenimines. Rearrangement of the oxoketenimines to imidoylketenes and cyclization afford the quinolones.


Acknowledgement

The present work was supported by the Australian Research Council.


References


[1]   (a) Andriole V., The Quinolones 2000 (Academic Press: New York, NY).
       (b) Fluoroquinolone Antibiotics (Eds Ronald A. R., Low) D. E. 2003 (Birkhäuser: Basel).

[2]   L. M. Jarvis, Chem. Eng. News 2008, 86,  15.
         
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
         open url image1

[19]   Kleeman H.-W., Carry J.-C., Desmazeau P., Mignani S., Bouquerel J., Genevois-Borella A., Ronan B., Aventis Pharma GMBH, PCT Int. Appl. WO2004007480, 22 January 2004.

[20]   Karabelas K., Lepisto M., Sjo P., Astrazeneca A. B., PCT 2000, SE00, WO0071537.